3-Nitro, 4-hydroxyphenylarsonic acid

The compound is odorless with a faintly acidic taste it is practically insoluble in water, ethanol and dilute acids but freely soluble in dilute aqueous alkaU with dissociation constants, pfC, 3.73, 7.9, 9.3. The compound is prepared by sodium hydrosulfite reduction of 3-nitro-4-hydroxyphenylarsonic acid [121 -19-7] and then acetylation in aqueous suspension with acetic anhydride at 50—55°C for 2 h (174,175). 

Arsonic and arsinic acids have found a number of industrial uses. They have been used as corrosion inhibitors for iron and steel, additives to motor fuel, agricultural bactericides, herbicides, and fungicides. 3-Nitro-4-hydroxyphenylarsonic acid (roxarsone) [121 -19-7] C H AsNOg, has found widespread use as an additive to poultry feed for the control of coccidiosis and other poultry diseases (122,123). Arsanilic acid [98-50-0] C HgAsNO, has also been used for this purpose (124) and for growth promotion in swine. It is manufactured and suppHed by Duphar Nutrition Co., Inc., Fleming Laboratories, Inc., Dr. Mayfield Laboratories, Inc., and Whitmoyer Laboratories, Inc. 4-Nitrophenylarsonic acid [98-72-6] C H AsNO and... 

Various phenylarsonic acids — especially arsanilic acid, sodium arsanilate, and 3-nitro-4-hydroxyphenylarsonic acid—have been used as feed additives for disease control and for improvement of weight gain in swine and poultry for almost 40 years (NAS 1977). The arsenic is present as As+5... 

The major class of compounds used as growth promotants in non-ruminant (single stomached) animals, such as pig and poultry, is that of the antimicrobials. Growth responses to antimicrobials were reported as early as 1946 but these findings were overlooked at the time. However, several years later, when growth responses were obtained with chlor-tetracycline, streptomycin (29), succinyl sulfathiazole and 3-nitro-4-hydroxyphenylarsonic acid, the practical aspects of growth responses to antimicrobials became clear. Since then, hundreds of antimicrobial compounds that promote growth have been reported in the scientific literature and in patents and many have been approved for use commercially. 

One hundred and forty-four grams (0.60 mole) of the dry mono-sodium salt of p-hydroxyphenylarsonic acid [Org. Syntheses Coll. Vol. 1, 490 (1941)] is added portionwise with stirring and cooling to 450 ml. of concentrated sulfuric acid. A mixture of 39 ml. of nitric acid (sp. gr. 1.4) and 39 ml. of concentrated sulfuric acid is added with continuous stirring and sufBcient cooling to hold.the temperature of the reaction mixture below 0°. The temperature is then allowed to rise to 10° over a period of several hours. The reaction mixture is poured into 2250 ml. of water and allowed to stand for 24-48 hours. The precipitated 3-nitro-4-hydroxyphenylarsonic acid is filtered off and washed with saturated aqueous sodium chloride solution until free of sulfuric acid and then with water until free of salt. The dry product is obtained in a yield of 65-75%. 

Nitro-4-hydroxyphenylarsonic acid 38 m-Hydrox3T)henylarsonic acid 0... 

Several arsenic compounds have been used in veterinary medicine. Arsenilic acid (C HgAsNOj) was used to treat swine dysentery, and arsenamide (CnHijAsNOjSj) for heartworm infection in dogs. Roxarsone (3-nitro-4-hydroxyphenylarsonic acid) is still extensively used in the feed of broiler poultry to control coccidial intestinal parasites, improve feed efficiency, and promote rapid growth, and there is no indication that it will be soon replaced by another drug. 

Various phenylarsoiuc acids - especially arsanilic acid, sodium arsanilate, and 3-nitro-4-hydroxyphenylarsonic acid-have been used as feed additives for disease control and for improvement of weight gain in swine and poultry for more than 50 years. The arsenic is present as As" " and is rapidly excreted present regulations require withdrawal of arsenical feed additives 5 days before slaughter for satisfactory depuration. Under these conditions, total arsenic residues inedible tissues do not exceed the maximum permissible limit of 2.0 mg/kg FW. Organoarseiucals probably will continue to be used as feed additives unless new evidence indicates otherwise. 

Synonyms Arsonic acid, (4-hydroxy-3-nitrophenyl)- 4-Hydroxy-3-nitrobenzenearsonic acid 2-Nitro-1-hydroxybenzene-4-arsonic acid 3-Nitro-4-hydroxybenzenearsonic acid 3-Nitro-4-hydroxyphenylarsonic acid Nitrophenoloarsonic acid Empirical CeHeAsNOe Formula HOC6H3(N02)AsO(OH)2 Properties Pale yel. cryst. or It. tan powd. sol. in methanol, acetic acid, alkalis, DMSO sol. 10-50 mg/ml in 95% ethanol sparingly sol. in dil. min. acids sol. < 1 mg/ml in water, acetone insol. in ethyl acetate, ether m.w. 263.04 m.p. > 300 C Toxicology ACGIH TLV/TWA 0.2 mg(As)/m ... 

Nitro-4-hydroxyphenylarsonic acid. See4-Hydroxy-3-nitrophenyl arsonic acid... 

Several MAE methods have also been developed for extraction of organometal compounds such as 3-nitro-4-hydroxyphenylarsonic acid and methyl-mercury from sediments and animal tissues. The MAE recoveries were consistently higher than those achieved with sonication or Soxhlet extraction. All species recoveries were matrix-dependent, as previously found with other pollutants, but using methanol acidified with acetic acid under optimal MAE conditions afforded rapid, efficient extraction of all analytes. 

An example of an arsenobenzene which is apparently a long chain polymer is Salvarsan or Arsphenamine. This results from reduction of 3-nitro-4-hydroxyphenylarsonic acid. 

Nitro-4-hydroxyphenylarsonic acid Roxarsone CjNsAsNOs 121-19-7 263.037 ye nd or pi (w) 300 slhotH20 ieth,Et0Ac vsMe0H, EtOH... 

Organic arsenicals such as arsenilic acid, 3-nitro-4-hydroxyphenylarsonic acid, 4-nitrophenylarsonic acid, and p-ureidobenzenearsonic acid have been used as a feed additive since the 1950 s [4]. The U.S. Food and Administration approves of all four of these compounds for use in poultry and swine feeds but only at levels low enough to preclude residues in edible animal tissues which would be hazardous to human health [10]. In France and other countries almost all uses of these compounds are forbidden. 

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